CA2535039A1 - Production process of optically pure 2-(4-hydroxyphenoxy)-propionic acid compounds - Google Patents
Production process of optically pure 2-(4-hydroxyphenoxy)-propionic acid compounds Download PDFInfo
- Publication number
- CA2535039A1 CA2535039A1 CA002535039A CA2535039A CA2535039A1 CA 2535039 A1 CA2535039 A1 CA 2535039A1 CA 002535039 A CA002535039 A CA 002535039A CA 2535039 A CA2535039 A CA 2535039A CA 2535039 A1 CA2535039 A1 CA 2535039A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- salt
- hydroxyphenoxy
- reducing agent
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical class OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 title 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 7
- 238000006243 chemical reaction Methods 0.000 claims abstract 3
- 239000003638 chemical reducing agent Substances 0.000 claims 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- AQIHDXGKQHFBNW-ZCFIWIBFSA-N (2r)-2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-ZCFIWIBFSA-N 0.000 claims 3
- 239000005498 Clodinafop Substances 0.000 claims 2
- 239000005502 Cyhalofop-butyl Substances 0.000 claims 2
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims 2
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 claims 2
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 claims 2
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 claims 2
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 claims 2
- 150000002429 hydrazines Chemical class 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 125000005216 haloheteroaryl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 235000010269 sulphur dioxide Nutrition 0.000 claims 1
- 239000004291 sulphur dioxide Substances 0.000 claims 1
- GXEMMZPHKGLVPF-SECBINFHSA-N (2R)-2-hydroxy-2-phenoxypropanoic acid Chemical compound O[C@](C(=O)O)(C)OC1=CC=CC=C1 GXEMMZPHKGLVPF-SECBINFHSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
A process for producing optically pure R-hydroxyphenoxypropanoic acid or a salt or ester thereof by reaction of hydroquinone or a salt thereof with an S- halopropanoic acid or a salt thereof in the presence of a mild reducing agen t.
Claims (7)
1. A process for producing R-2-(4-hydroxyphenoxy)propanoic acid or a salt thereof by reaction of hydroquinone or a salt thereof with a S-2-halopropanoic acid or a salt thereof in the presence of a mild reducing agent.
2. A process according to claim 1 wherein the S-2-halopropanoic acid is S-2-chloropropanoic acid.
3. A process according to claim 1 or claim 2 wherein the excess hydroquinone is recovered for recycle.
4. A process according to any preceding claim wherein the mild reducing agent is a neutral or a charged low oxidation state sulphur species, a low oxidation state phosphorous species, hydrazine, a hydrazine derivative or ascorbic acid.
5. A process according to claim 4 wherein the mild reducing agent is sulphur dioxide, a sulphite, a bisulphite, a hydrosulphite, a metabisulphite, a sulphinic acid, a sulphinic acid,,a phosphate, hypophosphite, hydrazine, a hydrazine derivative or ascorbic acid.
6. A process according to claim 5 wherein the mild reducing agent is an alkali metal sulphite or bisulphate.
7. A process for the manufacture of quizalofop-P-ethyl, haloxyfop-P-methyl, fluazifop-P-butyl, clodinafop, cyhalofop-butyl or fenoxaprop-P-ethyl by a) producing R-2-(4-hydroxyphenoxy)propanoic acid by reaction of hydroquinone or a salt thereof with S-2-halopropanoic acid or a salt thereof, in the presence of a mild reducing agent, b) reacting the R-2-(4-hydroxyphenoxy)propanoic acid with the appropriate halo-aryl or halo-heteroaryl moiety to give a R-2-((4-aryloxy or heteroaryloxy)phenoxy)propanoic acid and c) esterification of the acid from step b) to give quizalofop-P-ethyl, haloxyfop-P-methyl, fluazifop-P-butyl, clodinafop, cyhalofop-butyl or fenoxaprop-P-ethyl.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0322917.6 | 2003-09-30 | ||
| GBGB0322917.6A GB0322917D0 (en) | 2003-09-30 | 2003-09-30 | Chemical process |
| PCT/GB2004/003497 WO2005042460A1 (en) | 2003-09-30 | 2004-08-16 | Production process of optically pure 2- (4-hydroxyphenoxy) - propionic acid compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2535039A1 true CA2535039A1 (en) | 2005-05-12 |
| CA2535039C CA2535039C (en) | 2012-06-26 |
Family
ID=29415251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2535039A Active CA2535039C (en) | 2003-09-30 | 2004-08-16 | Production process of optically pure 2-(4-hydroxyphenoxy)-propionic acid compounds |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7268249B2 (en) |
| EP (1) | EP1670743B1 (en) |
| JP (2) | JP4965256B2 (en) |
| KR (1) | KR101102822B1 (en) |
| CN (1) | CN100422129C (en) |
| AT (1) | ATE353868T1 (en) |
| BR (1) | BRPI0414925B1 (en) |
| CA (1) | CA2535039C (en) |
| DE (1) | DE602004004810T2 (en) |
| DK (1) | DK1670743T3 (en) |
| EA (1) | EA009241B1 (en) |
| ES (1) | ES2282897T3 (en) |
| GB (1) | GB0322917D0 (en) |
| IL (1) | IL173524A (en) |
| PL (1) | PL1670743T3 (en) |
| PT (1) | PT1670743E (en) |
| TW (1) | TWI343911B (en) |
| WO (1) | WO2005042460A1 (en) |
| ZA (1) | ZA200601145B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467452C (en) * | 2006-11-01 | 2009-03-11 | 浙江工业大学 | Method for preparing haloxyfop-P-methyl with high optic purity |
| CN101835742A (en) * | 2007-10-24 | 2010-09-15 | 陶氏益农公司 | Improved process for the manufacture of r-(+)-2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propionic acid esters |
| CN102391104A (en) * | 2011-09-16 | 2012-03-28 | 南通嘉禾化工有限公司 | Process for synthesizing and separating (R)-(+)-2-para hydroxyphenoxypropionic acid |
| CN102584691A (en) * | 2012-01-12 | 2012-07-18 | 南京红太阳生物化学有限责任公司 | Novel method for synthetizing clodinafop-propargyl |
| DE102016221270B4 (en) * | 2015-11-30 | 2019-03-21 | Ford Global Technologies, Llc | Mobile transport device, vehicle and method for moving a mobile transport device |
| CN111187155B (en) * | 2020-03-25 | 2022-04-05 | 江苏三吉利化工股份有限公司 | Method for synthesizing R- (+) -2- (4-hydroxyphenoxy) propionic acid by gas phase catalysis |
| JP2023027630A (en) * | 2021-08-17 | 2023-03-02 | 住友化学株式会社 | Method for producing ether compound |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR763374A (en) * | 1933-01-23 | 1934-04-30 | Manuf De Prod Chim Purs | Process for the preparation of optical antipodes of bodies endowed with rotary power |
| JPS5616475A (en) * | 1979-07-19 | 1981-02-17 | Nissan Chem Ind Ltd | Quinoxaline derivative and herbicide containing the same as effective component |
| US4505743A (en) * | 1981-12-31 | 1985-03-19 | Ciba-Geigy Corporation | α-[4-(3-Fluoro-5'-halopyridyl-2'-oxy)-phenoxy]-propionic acid derivatives having herbicidal activity |
| DE3240805A1 (en) * | 1982-11-05 | 1984-05-10 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING HYDROXY-PHENOXY ALKANCARBONIC ACIDS |
| US4505753A (en) * | 1983-06-30 | 1985-03-19 | Research One Limited Partnership | Cementitious composite material |
| JPS60123443A (en) * | 1983-12-07 | 1985-07-02 | Nissan Chem Ind Ltd | Production of 2-(4-hydroxyphenoxy)alkanoic acid |
| JPH0610154B2 (en) * | 1984-12-28 | 1994-02-09 | 日産化学工業株式会社 | Process for producing optically active 2- (4-hydroxyphenoxy) propionic acid |
| FR2634481B1 (en) * | 1988-07-20 | 1990-09-14 | Rhone Poulenc Chimie | PROCESS FOR THE PURIFICATION OF D-HYDROXYPHENOXYPROPIONIC ACID |
| JP2514072B2 (en) * | 1988-07-20 | 1996-07-10 | ダイセル化学工業株式会社 | Process for producing optically active 2- (4-hydroxyphenoxy) propionic acid |
| JPH02268134A (en) * | 1989-04-11 | 1990-11-01 | Tosoh Corp | Preparation of optically active 2-(4-hydroxyphenoxy) propionic acid |
| JPH08134018A (en) * | 1994-11-04 | 1996-05-28 | Nippon Green Consultant Kk | Production of 3-(2-hydroxyphenoxy)propionic acid derivative |
-
2003
- 2003-09-30 GB GBGB0322917.6A patent/GB0322917D0/en not_active Ceased
-
2004
- 2004-08-16 KR KR1020067006076A patent/KR101102822B1/en active IP Right Grant
- 2004-08-16 US US10/571,863 patent/US7268249B2/en active Active
- 2004-08-16 WO PCT/GB2004/003497 patent/WO2005042460A1/en active IP Right Grant
- 2004-08-16 EA EA200600496A patent/EA009241B1/en not_active IP Right Cessation
- 2004-08-16 PL PL04768060T patent/PL1670743T3/en unknown
- 2004-08-16 BR BRPI0414925-4A patent/BRPI0414925B1/en active IP Right Grant
- 2004-08-16 CN CNB2004800267093A patent/CN100422129C/en active Active
- 2004-08-16 JP JP2006530547A patent/JP4965256B2/en active Active
- 2004-08-16 CA CA2535039A patent/CA2535039C/en active Active
- 2004-08-16 EP EP04768060A patent/EP1670743B1/en active Active
- 2004-08-16 ES ES04768060T patent/ES2282897T3/en active Active
- 2004-08-16 DK DK04768060T patent/DK1670743T3/en active
- 2004-08-16 DE DE602004004810T patent/DE602004004810T2/en active Active
- 2004-08-16 PT PT04768060T patent/PT1670743E/en unknown
- 2004-08-16 AT AT04768060T patent/ATE353868T1/en active
- 2004-08-30 TW TW093126006A patent/TWI343911B/en active
-
2006
- 2006-02-02 IL IL173524A patent/IL173524A/en active IP Right Grant
- 2006-02-08 ZA ZA200601145A patent/ZA200601145B/en unknown
-
2011
- 2011-08-01 JP JP2011168718A patent/JP2011236244A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TW200512185A (en) | 2005-04-01 |
| ZA200601145B (en) | 2007-05-30 |
| DE602004004810T2 (en) | 2007-12-06 |
| JP4965256B2 (en) | 2012-07-04 |
| EP1670743B1 (en) | 2007-02-14 |
| PT1670743E (en) | 2007-03-30 |
| KR101102822B1 (en) | 2012-01-05 |
| ATE353868T1 (en) | 2007-03-15 |
| IL173524A0 (en) | 2006-07-05 |
| US20060270851A1 (en) | 2006-11-30 |
| WO2005042460A1 (en) | 2005-05-12 |
| DK1670743T3 (en) | 2007-05-29 |
| CN1852884A (en) | 2006-10-25 |
| GB0322917D0 (en) | 2003-11-05 |
| EA200600496A1 (en) | 2006-10-27 |
| CN100422129C (en) | 2008-10-01 |
| BRPI0414925B1 (en) | 2014-02-18 |
| ES2282897T3 (en) | 2007-10-16 |
| KR20060094954A (en) | 2006-08-30 |
| DE602004004810D1 (en) | 2007-03-29 |
| EP1670743A1 (en) | 2006-06-21 |
| EA009241B1 (en) | 2007-12-28 |
| IL173524A (en) | 2010-11-30 |
| US7268249B2 (en) | 2007-09-11 |
| BRPI0414925A (en) | 2006-11-07 |
| TWI343911B (en) | 2011-06-21 |
| JP2007507478A (en) | 2007-03-29 |
| PL1670743T3 (en) | 2007-06-29 |
| CA2535039C (en) | 2012-06-26 |
| JP2011236244A (en) | 2011-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |